Diisopropylethylamine → 2-(1-(3-(Trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(O)=O.[NH:22]1[CH2:27][CH2:26][CH:25]([O:28][N:29]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]2=[O:39])[CH2:24][CH2:23]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([S:9]([N:22]2[CH2:27][CH2:26][CH:25]([O:28][N:29]3[C:30](=[O:39])[C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:37]3=[O:38])[CH2:24][CH2:23]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(Trifluoromethyl)benzenesulfonyl chloride (3.23 g, 13.2 mmol) was added to a solution of 2-(piperidin-4-yloxy)isoindoline-1,3-dione trifluoroacetic acid (3.56 g, 9.80 mmol) and N,N-diisopropylethylamine (7.10 g, 55.0 mmol) in CH2Cl2 (85 ml), and stirred at room temperature for 17 hours. The reaction mixture was washed with aqueous 1 N HCl solution (20 ml×3), aqueous NaHCO3 solution (20 ml×3), brine (20 ml×2), dried over Na2SO4, filtered and concentrated in vacuo to give 2-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yloxy)isoindoline-1,3-dione (4.12 g, 93%) as a white solid: LCMS: 454 [M+1]+.
Workup
- washThe reaction mixture was washed with aqueous 1 N HCl solution (20 ml×3), aqueous NaHCO3 solution (20 ml×3), brine (20 ml×2)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0ed696eadb294aa28429dd3271a297fb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518934B2
Reaction notes
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